


Learning to Fly

by chucks_prophet



Category: Supernatural
Genre: Abusive John Winchester, Angst and Hurt/Comfort, Angst with a Happy Ending, Benny Lafitte & Dean Winchester Friendship, Best Friends, Cancer, Dean Winchester and Feelings, Excessive Drinking, Friends to Lovers, Gay Castiel, Heavy Angst, Implied/Referenced Alcohol Abuse/Alcoholism, John Winchester's A+ Parenting, M/M, Redeemed John Winchester, Sam is the Voice of Reason
Language: English
Status: Completed
Published: 2015-11-24
Updated: 2015-11-24
Packaged: 2018-05-03 03:11:18
Rating: Mature
Warnings: Major Character Death
Chapters: 1
Words: 3,082
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5274350
Author URL: https://archiveofourown.org/users/chucks_prophet/pseuds/chucks_prophet
Summary: <blockquote class="userstuff">
              <p>The first time it happened, Sam left for Stanford.</p><p>Not that Dean could leave home for some hoity toity prep school. Sam was the son of John’s affection; Dean was his infliction. He made that clear when he pinned Dean against the wall and told him to get out.</p><p>John was always a depressive drunk. In a weird way, it was a step up from his usual ways.</p><p>Dean could’ve fought back, seeing as he had at least fifty pounds on him since John went on his mission to find God at the bottom of every Blue Moon, but that would’ve meant John going after Sam. And by his God, Dean was not gonna let that happen. Someone in this family was going to exercise their right to a happily ever after, should that mean swearing allegiance to a life of torment and turbulence, Dean would just have to live with the consequences. It’s not like he stood a shot at anything extraordinary, anyway.</p><p>Title and lyrics by Tom Petty.</p>
            </blockquote>





	Learning to Fly

Learning to Fly

_I'm learning to fly, but I ain't got wings_

_Coming down is the hardest thing_

_Well the good ol' days may not return_

_And the rocks might melt and the sea may burn_

The first time it happened, Sam left for Stanford.

Not that Dean could leave home for some hoity toity prep school. Sam was the son of John’s affection; Dean was his _inflict_ ion. He made that clear when he pinned Dean against the wall and told him to get out.

John was always a depressive drunk. In a weird way, it was a step up from his usual ways.

Dean could’ve fought back, seeing as he had at least fifty pounds on him since John went on his mission to find God at the bottom of every Blue Moon, but that would’ve meant John going after Sam. And by _his_ God, Dean was not gonna let that happen. Someone in this family was going to exercise their right to a happily ever after, should that mean swearing allegiance to a life of torment and turbulence, Dean would just have to live with the consequences. It’s not like he stood a shot at anything extraordinary, anyway.

Or maybe he did. It was hard to tell, seeing as every accomplishment Dean’s ever had has been coupled—or _shrouded,_ depending on who you asked—by one of John’s misfortunes.

January 24, 1979, the day Dean was brought into the world, was the day his mother’s body was masked by a white sheet. Five years later when he made Little League, John lost his job at the factory. Another five years later, when Dean met his new little brother for the first time, John’s do-over wife, Tara, filed for divorce.

When Dean graduated valedictorian, John graduated to whiskey. A few of Dean’s closest friends invited him to a celebratory night at his place, but the only thing Dean could think about was how hammered John was getting at home. He couldn’t leave Sammy alone.

More recently, Dean represented one Sam Wesson at Stanford Law’s Graduating Ceremony. Not even John showing up completely wasted could wipe the tears from Dean’s eyes. Dean sent John in an Uber back to their motel and treated Sam and his fiancée, Jess, to dinner.

Despite growing up in a toxic environment—despite the statistical odds stacked against him—Sammy became the man neither he nor John could ever be. Dean couldn’t have been more proud.

“Dean, are you okay?”

Dean snapped his focus to the man in front of him. His deep cerulean eyes poked out of the upturned lapels on his wonted trenchcoat. His dark hair—a stark contrast from what Dean jokes was a ‘vampiric’ skin tone—was sticking out like a needle on a busted compass. Dean knew the look all too well; he chased sleep like a coonhound that hunted during the day. “Yeah, just, uh… zoned out for a moment s’all.”

Castiel hailed the waiter. “One check, please.”

“Cas—”

“Dean,” he interjected, fishing out his wallet from his left coat pocket, “I don’t mind. Honestly.”

“I don’t care if you don’t mind, _I_ mind, man.”

Cas leveled his gaze with Dean’s. “Dean, let someone do something for you for a change.”

They headed for Castiel’s ’78 Continental not before Dean slipped the waiter a twenty.

***

The following week, it was Dean who was on the receiving end of the bad news.

John was diagnosed with liver cancer.

Sam flew in upon hearing the news. For the first time in six years, the family was reunited, and John was sobered up—at least until after the brothers left the house for a split second, leaving John to raid the fridge. When they came back inside, John shot a pointed look at his sons. “Why the hell’s he here?”

Sam was, mistakenly, the one to chime in first, “It’s Cas, Dad, he’s family.”

John wobbled to the kitchen table with a bottle in hand. “I don’t care’f he takes it up the ass, he’s _not_ family.”

“Dad, put that down,” Sam said tentatively.

“It’s too late for me, son. Another beer won’t hurt me anymore than it already has.”

“Let’s go, man,” Dean murmured to Cas through gritted teeth, guiding the shorter man out of the house.

He hid a scowl he was sure would stay that way behind the collar of his jean jacket. Straying away from the constant stench of body odor and pissed away dreams might do them good anyway. “Sorry, you didn’t deserve that. I shouldn’t have brought you here, it’s my fucking fault; it’s always my fucking—”

“Dean—”

Dean was running in dizzying circles on the front porch. “—Mom’s death, that’s on me, Sam wants to go to college, sorry _,_ Dad’s constipated for a week, _my bad—”_

“ _Dean.”_

“I’m barely holding down the fort, and he’s gotta go and get fucking cancer! Who’s gonna pay for that? He’ll bleed Sammy dry, then what, blame himfor his sickness? _I_ wiped his ass and paid his rent and made him a greasy breakfast. I mean, the bacon was always a little burnt and the eggs were a little soggy, but the toast was never—”

Blessedly, Cas took him in his arms, effectively shutting him up. Dean didn’t realize he was crying until a sob climaxed in his throat, choking him like a phantom killer. For all he cared, he could suffocate himself on Cas’s scent and his stupid trenchcoat. But Cas wouldn’t let him with gentle hands on his back and fingers acting as a comb, working out the knots in his mocha hair, which unquestionably needed a haircut and a shower.

Needless to say, he barely heard Cas whisper, “Let’s take a walk.”

***

"Do you remember when we first met?"

The houses that lined the block, like the face of humanity, were heterogeneous. Some were big, others small. Some were one solid color; others strive to keep Home Depot in business. The same goes for the passing cars. Some filled the untenanted setting with pulsations of their culture, others nothing more than a thin trail of cancer. It’s been a while since Dean’s strolled down the old neighborhood, despite how often he was there.

He chuckled, breathing out the scent of Martin Creaser’s newly irrigated lawn. "'Course I do, you were a doe-eyed college student coming into the shop with that fucking Mark Five—"

"Hey, she's still a classic!" Cas contended.

"—that was practically spitting lettuce from the exhaust pipe," Dean chuckled lightly, shouldering him just so. "I tried to convince you to sack it, but you insisted on keeping the thing, so I told you to come back in a week and I'd see what I could do."

"And then I came back for more than just a week..."

“Bobby thought we were dating!" Dean laughed with the shake of his head.

"In all fairness, you _did_ try to kiss me once."

" _I_ _tripped over a carburetor_."

"Yeah, well, for the record, I didn't want to kiss you back." Dean shouldered him again, adding a little elbow. After a few more steps, Cas pivoted to face Dean. "You were the first person I came out to."

"You too."

Castiel always had a way of looking into Dean without actually _looking_ at him. Maybe it was their unparalleled “bond” Cas spoke of (the dude was big into astrology and shit like that), but his gaze was just over Dean’s shoulder and he could feel an immense weight lifted from there.

The wind blew the opposite direction, blowing Castiel’s stupidly messy hair like a flag at half-mass as he asked, “Do you want to head back?”

“Nah,” Dean replied, lips turning up in a small smile. “Let’s keep going.”

***

For the remainder of the year, it wasn’t atypical for John’s daily diatribe to be short by the “fucking party” in his abdomen, or for him to pick at his food rather than bang his fists on the table. The combination of the two caused the laugh lines around his dull, brown eyes to permanently pleat and most of his wardrobe to look like maternity clothes.

But nothing compared to the prolonged silence that haunted the house day in and day out. Dean would give anything to be slammed against a wall again just to _hear_ something… _feel_ something other than the constant uncertainty of Death’s upraised scythe.

Sam returned to Lawrence after the ball dropped, said his workload was unforgiving, even though Jessica offered to take the night shifts at the hospital. They had multiple dinners in his bedroom with _Jerry Springer_ blaring at a ridiculous volume. After the fifth dinner, Sam suggested they migrate to the living room. John didn’t budge. The closest they got to going out was a milk run at the local mart where they bumped into Tara, John’s ex-wife. That seemed to elicit some reaction out of John’s droopy, basset hound-akin stare… until a man wrapped his arms around her middle.

John made a habit out of closing his bedroom door after that.

“Should we have gone with the treatment plan?” Sam asked him over lunch at Biggerson’s one day.

Dean left fingerprints in his bun and eventually just stuck with his fries. “Would it’ve mattered?”

Sam masked a plaintive frown in a forkful of dried greens and that was the end of that discussion.

Dean kept working to keep his unattended apartment afloat and didn’t accept pity from anyone—least of all himself. Dean couldn’t _afford_ to sulk. The only thing he accepted was the overtime. Working underneath cars was a therapeutic experience, as weird as it may have sounded. Keeping his hands busy meant keeping his mind busy, which was a godsend nowadays.

“S’cuse me, ya’ll do boat repairs? My engine stalls like the Devil in Hell.”

Dean pushed his creeper out from underneath him, “Benny Fucking Lafitte.” He enveloped the man in a classified bro-hug—not one, but two hand clasps followed by a one-handed hug.

He braced an oily palm on Benny’s broad shoulder, eyeing all two-hundred pounds of him with a raised brow. “I see the high seas haven’t shaken your girlish figure.”

“How ‘bout that, fifteen years and you’re still a smart ass.”

“I learned from the best,” Dean acknowledged with a wink, wiping his hands and leaning against the hood of the Focus. He wanted to offer him a cold one, but only kept bottled water and iced tea in his cooler. “What in the hell brings you to back to Lawrence? I thought you’d be halfway across the Portland Canal with that Greek Goddess of yours by now."

“I _was,_ ” he admitted, scratching his orange and gray beard, “Till I heard ‘bout your ole man.”

Dean pursed his lips. “You and every other Tom, Dick, and Harry within the nearest payphone.”

“’m sorry, brotha, truly.”

“I know.” _You and every other Tom, Dick, and Harry…_

“I know how you take ta pity, but if there’s anything I can do, you holla at me.” Benny wore a sad smile, but his light blue eyes conveyed promise.

“There is something,” Dean admitted. “You still know your way around a wrench?”

Benny cracked a small smile as he scoffed, “Who do ya take me for?”

***

The letter Dean received was dated a week after Unattached Drifter Christmas:

_February 28, 2016_

_Dean Winchester_

_11056 W. Cainslay Ave._

_Lawrence, KS 66049_

_Dear Dean,_

_You have received this letter because you were hand-selected by our finest faculty and staff through the “Share Your Story” scholarship that expressed the applicant’s perspective on their life in a unique and creative fashion. It’s individuals like you that embody the driving force of the seminary and it is with pleasure that the University of Michigan in Ann Arbor hereby **grants you admission** into the class of 2021._

_It is a particularly exciting time to be an engineering student at the University of Michigan. You will be awarded the chance to work alongside some of the greatest minds in the industry, gaining hands-on experience and creating personal connections you will need to be successful in your field of study. With a success rate of 90.7%, it’s no wonder the University of Michigan in Ann Arbor was one of your secondary schooling choices._

_To receive this unparalleled opportunity, we advise that you enroll with us no later than March 18 for the fall semester. In addition, you will need to accept or deny the financial aid we’ve graciously offered you to attend the University of Michigan._

_We hope to see you on campus the week of August 22, 2016. In the meantime, have a fulfilling summer._

_Sincerely,_

**_Michael Novak_ **

_Dean of Admissions_

_and Financial Aid_

 

 

Dean read the letter once, twice, and backwards—he even pinched himself in the place he was most sensitive. Nope, he was still standing outside his old house (Dean had all his mail forwarded there since that’s where he spent the majority of his time) in a thin pair of PJs with the wind hitting his back not unlike a few one-nighters he picked up at the gay bar on Franklin.

This was actually happening. Dean “Six Bucks to His Name” Winchester got accepted into college.

Sam didn’t leave out any enthusiasm: _“You hear that, Jess? Our big brother is moving up in the world!”_

_“Ask him if the fellito he gave was—”_

_“We love him to pieces!”_ he heard Jess cut in for what couldn’t be mistaken for Charlie Bradbury’s voice. Dean remembered Sam telling him about her surprise visit—conveniently on the day a comic store opened near them.

He heard the shuffle of the phone as Sam switched ears. “ _You excited?”_

“I guess,” Dean said in a small voice, suddenly shy as his eye caught the faint outline of John’s silhouette in the living room. He kept his back hunched against the wall. He thought he heard a _click_ on his end, but it could’ve very well been his own paranoia. “I mean, it’s obviously an awesome opportunity and everything, but—”

“ _Dean, I love you, but I swear on my unborn children if you turn down them down I will personally drive over there and kick your six-foot one ass.”_

Though it still weighed heavy on his conscious, a lopsided grin masked any evidence of Dean’s growing doubt. “Bitch.” 

“ _Jerk_.”

Dean hung up, peered around the corner to see his father loosely clutching the other landline phone. Slowly, he emerged from the shadows of the crypt-like house and approached John, who wore a look so impassive Kristen Stewart would have a hard time rivaling it. This time, his head was angled toward the shit-stained blinds on the other side of the room.

“I’m sorry, okay? Is that what you wanna hear?” Dean blurted. There were no tears, no shakiness in his tone, just long overdue words spilling out of his mouth like a busted dam. “I’m sorry for costing you the best job in the world, letting your affair with Adam Milligan’s mother slip to Tara, sending in Sam’s application a year early, but I’m not sorry I'm more accomplished than you. I will _never_ apologize for that.”

Dean didn’t have time to see the grave expression on his father’s face. He swiped his jacket from the couch and left without saying goodbye.

***

“Dean? What’re you do—?”

Dean didn’t give him a chance to finish because his lips were on Castiel’s. Cas froze against him before his hands rested on both sides of his face, acted as a vice, succumbing him further into his sinful mouth. For a second, Dean forgot _he_ was the one who made the impulsive move.

Despite looking seven ways fucked beside his own doorway, Cas was the first to pull away with the same question on his tongue: “What’re you doing?”

“Making my own decisions,” he replied breathlessly, letting their torsos press together like two hot irons. Cas’s lust-laden eyes came into focus with one slow blink, a ruby-red blush adding color to his cheeks. Dean never realized how gorgeous he was—especially in as little clothing as he was in now.

“Which include?” Cas teased, the corner of his lip quirking up.

Dean hummed against his forehead, “You, me, and the University of Michigan.”

“You don’t mean—?”

“I do,” he confirmed, grinning like he hasn’t grinned in years, “I really, _really_ do.”

Cas threw his arms around him, pulling him into a tight hug. “Oh my God. _You did it._ I knew you could do it.”

Dean held him back with everything he had, because everything he had—everything he ever needed—was beneath his fingers. “You were telling me how I need to let someone do something for me,” he whispered, beating each syllable against the tuff of hair around his right ear. “I’d like to take you up on that offer now.”

***

John died January 21, 2021, three days short of Dean’s 42nd birthday. He would’ve held out for the birth of his second grandson, Jonathan Wesson, if he’d have put down the bottle sooner.

Nonetheless, Dean was proud to share his birthday with his father’s reincarnation.

The reception was beautiful, complete with a military salute and everything. Dean wore the suit he never got to wear to his senior prom, smiling upon seeing his father surrounded by hundreds of adoring fans—including his mother, who sat next to him in a golden urn on Dean’s mantle.

He and his brother spent an overdue Christmas and New Year’s together. John Jr., on the other hand, spent most of his belated holidays in moose antlers—something Sammy thought was apropos if he was planning on outgrowing his father one day, and Jess and Dean thought was just plain ridiculous.

His fiancé, Cas, mingled with his future best man, Benny, undoubtedly swapping tongue-in-cheek moments about their shared best friend. Dean pretended not to notice Benny leaning into Cas and overhear him saying something about kicking his ass if Dean gave Cas any trouble.

Dean smiled, taking in the scene as he clutched his warm eggnog. Someone in this family was going to exercise their right to a happily ever after, should that mean swearing allegiance to a life of love and commitment, Dean would just have to live with the consequences.

**-END-**

_Well some say life will beat you down_

_Break your heart, steal your crown_

_So I've started out for God knows where_

_I guess I'll know when I get there_


End file.
